Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Simon A. Llewellyn' _publ_contact_author_address ;Inorganic Chemistry Department South Parks Rd Oxford OX13QR ; _publ_contact_author_email simon.llewellyn@chem.ox.ac.uk _publ_contact_author_phone +441865272600 loop_ _publ_author_name _publ_author_address S.Llewellyn ;Inorganic Chemistry Department South Parks Rd Oxford OX13QR ; M.L.H.Green ;Inorganic Chemistry Department South Parks Rd Oxford OX13QR ; A.R.Cowley ;Chemistry Research Laboratory Mansfield Rd Oxford OX13DA ; _publ_section_title ; Cobalt N-heterocyclic carbene alkyl and acyl compounds: synthesis, molecular structure and reactivity ; data_arc1011 _database_code_depnum_ccdc_archive 'CCDC 291790' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_special_details ; The hydrogen atoms of the methyl ligand were located in a difference Fourier map and their coordinates and isotropic displacement parameters subsequently refined. All other H atoms were positioned geometrically, the preferred orientations of the methyl substituents of the mesityl groups having been determined by previous examination of the Fourier map ; #============================================================= _cell_length_a 7.8826(2) _cell_angle_alpha 101.1593(12) _cell_length_b 8.5076(3) _cell_angle_beta 90.3479(13) _cell_length_c 18.9876(7) _cell_angle_gamma 109.8209(16) _cell_volume 1171.71(7) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'Co ' 0.3494 0.9721 12.2841 4.2791 7.3409 0.2784 4.0034 13.5359 2.3488 71.1692 1.0118 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C25 H27 Co N2 O3 ' _chemical_formula_moiety ' C25 H27 Co N2 O3 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 462.43 _cell_measurement_reflns_used 16259 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' pale yellow ' _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_max 0.36 _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.760 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 0.96 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 16259 _reflns_number_total 5289 _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_theta_min 5.209 _diffrn_reflns_theta_max 27.472 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.472 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min -11 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _refine_diff_density_min -0.39 _refine_diff_density_max 0.36 _refine_ls_number_reflns 3655 _refine_ls_number_restraints 0 _refine_ls_number_parameters 284 #_refine_ls_R_factor_ref 0.0377 _refine_ls_wR_factor_ref 0.0439 _refine_ls_goodness_of_fit_ref 1.0869 #_reflns_number_all 5289 _refine_ls_R_factor_all 0.0644 _refine_ls_wR_factor_all 0.0585 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 3655 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_gt 0.0439 _refine_ls_shift/su_max 0.002429 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.12 0.343 0.793 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type Co1 Co 0.51090(4) 0.36314(4) 0.253115(17) 0.0258 1.0000 Uani C1 C 0.2490(3) 0.2413(3) 0.23823(12) 0.0239 1.0000 Uani N1 N 0.1315(3) 0.1853(2) 0.28815(10) 0.0269 1.0000 Uani C2 C -0.0467(3) 0.1156(3) 0.25906(13) 0.0320 1.0000 Uani C3 C -0.0430(3) 0.1300(3) 0.18940(13) 0.0321 1.0000 Uani N2 N 0.1371(2) 0.2062(2) 0.17752(10) 0.0257 1.0000 Uani C4 C 0.1784(3) 0.1700(3) 0.35929(12) 0.0272 1.0000 Uani C5 C 0.1920(3) 0.3011(3) 0.41858(13) 0.0341 1.0000 Uani C6 C 0.2289(4) 0.2749(4) 0.48635(14) 0.0408 1.0000 Uani C7 C 0.2495(4) 0.1244(4) 0.49569(14) 0.0404 1.0000 Uani C8 C 0.2342(4) -0.0033(4) 0.43541(14) 0.0375 1.0000 Uani C9 C 0.1990(3) 0.0169(3) 0.36651(13) 0.0300 1.0000 Uani C10 C 0.1675(5) 0.4648(4) 0.40960(16) 0.0479 1.0000 Uani C11 C 0.2848(5) 0.0962(5) 0.57003(17) 0.0575 1.0000 Uani C12 C 0.1899(4) -0.1188(3) 0.30138(15) 0.0396 1.0000 Uani C13 C 0.1912(3) 0.2333(3) 0.10707(12) 0.0270 1.0000 Uani C14 C 0.1884(3) 0.3804(3) 0.08546(13) 0.0292 1.0000 Uani C15 C 0.2380(3) 0.4000(3) 0.01630(14) 0.0341 1.0000 Uani C16 C 0.2881(3) 0.2783(3) -0.03006(13) 0.0353 1.0000 Uani C17 C 0.2846(3) 0.1312(3) -0.00706(13) 0.0324 1.0000 Uani C18 C 0.2341(3) 0.1045(3) 0.06122(12) 0.0288 1.0000 Uani C19 C 0.1321(4) 0.5136(3) 0.13382(15) 0.0384 1.0000 Uani C20 C 0.3404(4) 0.3016(4) -0.10481(15) 0.0465 1.0000 Uani C21 C 0.2255(4) -0.0575(3) 0.08338(14) 0.0353 1.0000 Uani C22 C 0.7841(3) 0.5062(4) 0.27156(15) 0.0348 1.0000 Uani C23 C 0.4914(3) 0.5671(3) 0.26159(13) 0.0308 1.0000 Uani O1 O 0.4964(3) 0.7047(3) 0.26547(12) 0.0471 1.0000 Uani C24 C 0.5611(3) 0.2899(3) 0.33025(15) 0.0378 1.0000 Uani O2 O 0.6222(3) 0.2598(3) 0.37885(13) 0.0594 1.0000 Uani C25 C 0.5776(3) 0.2805(3) 0.16905(14) 0.0337 1.0000 Uani O3 O 0.6432(3) 0.2441(3) 0.11716(11) 0.0489 1.0000 Uani H1 H 0.809(4) 0.584(4) 0.3197(19) 0.048(9) 1.0000 Uiso H2 H 0.818(4) 0.573(4) 0.2371(18) 0.047(9) 1.0000 Uiso H3 H 0.856(5) 0.435(4) 0.2687(17) 0.046(8) 1.0000 Uiso H21 H -0.1561 0.0648 0.2846 0.0381 1.0000 Uiso H31 H -0.1494 0.0930 0.1534 0.0377 1.0000 Uiso H61 H 0.2409 0.3673 0.5296 0.0505 1.0000 Uiso H81 H 0.2489 -0.1120 0.4418 0.0482 1.0000 Uiso H101 H 0.1821 0.5422 0.4579 0.0606 1.0000 Uiso H102 H 0.2603 0.5223 0.3784 0.0606 1.0000 Uiso H103 H 0.0438 0.4383 0.3866 0.0606 1.0000 Uiso H111 H 0.1671 0.0394 0.5895 0.0747 1.0000 Uiso H112 H 0.3502 0.2087 0.6028 0.0747 1.0000 Uiso H113 H 0.3604 0.0218 0.5668 0.0747 1.0000 Uiso H121 H 0.2074 -0.2184 0.3169 0.0480 1.0000 Uiso H122 H 0.2871 -0.0715 0.2697 0.0480 1.0000 Uiso H123 H 0.0690 -0.1568 0.2741 0.0480 1.0000 Uiso H151 H 0.2376 0.5045 -0.0003 0.0401 1.0000 Uiso H171 H 0.3191 0.0425 -0.0404 0.0364 1.0000 Uiso H191 H 0.1395 0.6080 0.1084 0.0490 1.0000 Uiso H192 H 0.2145 0.5605 0.1789 0.0490 1.0000 Uiso H193 H 0.0050 0.4606 0.1462 0.0490 1.0000 Uiso H201 H 0.2292 0.2567 -0.1388 0.0517 1.0000 Uiso H202 H 0.4030 0.4258 -0.1040 0.0517 1.0000 Uiso H203 H 0.4236 0.2378 -0.1211 0.0517 1.0000 Uiso H211 H 0.2611 -0.1321 0.0432 0.0417 1.0000 Uiso H212 H 0.3102 -0.0300 0.1270 0.0417 1.0000 Uiso H213 H 0.0993 -0.1185 0.0947 0.0417 1.0000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.02363(15) 0.02602(16) 0.02740(16) 0.00722(11) 0.00098(10) 0.00724(11) C1 0.0249(10) 0.0221(10) 0.0261(10) 0.0077(8) 0.0027(8) 0.0084(8) N1 0.0250(9) 0.0286(9) 0.0276(9) 0.0088(8) 0.0028(7) 0.0084(8) C2 0.0248(11) 0.0351(12) 0.0354(13) 0.0118(10) 0.0019(9) 0.0072(10) C3 0.0226(11) 0.0354(12) 0.0362(13) 0.0097(10) -0.0008(9) 0.0064(9) N2 0.0242(9) 0.0269(9) 0.0257(9) 0.0079(7) 0.0011(7) 0.0072(7) C4 0.0266(10) 0.0316(11) 0.0249(10) 0.0108(9) 0.0039(8) 0.0093(9) C5 0.0374(13) 0.0377(13) 0.0305(12) 0.0090(10) 0.0068(10) 0.0161(11) C6 0.0475(15) 0.0512(16) 0.0275(12) 0.0075(11) 0.0029(10) 0.0221(13) C7 0.0398(14) 0.0574(17) 0.0312(13) 0.0204(12) 0.0067(10) 0.0199(13) C8 0.0360(13) 0.0430(14) 0.0415(14) 0.0224(11) 0.0090(11) 0.0163(11) C9 0.0265(11) 0.0293(11) 0.0356(12) 0.0130(9) 0.0064(9) 0.0081(9) C10 0.069(2) 0.0412(15) 0.0410(15) 0.0070(12) 0.0048(13) 0.0296(15) C11 0.062(2) 0.085(2) 0.0389(16) 0.0278(16) 0.0050(14) 0.0358(19) C12 0.0456(15) 0.0274(12) 0.0470(15) 0.0089(11) 0.0059(12) 0.0135(11) C13 0.0262(10) 0.0290(11) 0.0253(10) 0.0086(9) -0.0001(8) 0.0074(9) C14 0.0257(11) 0.0286(11) 0.0322(11) 0.0098(9) -0.0021(9) 0.0060(9) C15 0.0344(12) 0.0317(12) 0.0343(12) 0.0160(10) -0.0032(10) 0.0042(10) C16 0.0307(12) 0.0395(13) 0.0268(11) 0.0093(10) -0.0019(9) -0.0005(10) C17 0.0295(11) 0.0336(12) 0.0281(11) 0.0038(9) -0.0010(9) 0.0048(9) C18 0.0264(11) 0.0289(11) 0.0295(11) 0.0074(9) -0.0019(9) 0.0068(9) C19 0.0429(14) 0.0365(13) 0.0431(14) 0.0162(11) 0.0034(11) 0.0188(11) C20 0.0468(16) 0.0516(16) 0.0309(13) 0.0156(12) 0.0027(11) 0.0003(13) C21 0.0408(13) 0.0274(11) 0.0361(13) 0.005(1) -0.0002(10) 0.0107(10) C22 0.0262(12) 0.0350(13) 0.0381(14) 0.0066(11) 0.0007(10) 0.0049(10) C23 0.0272(11) 0.0307(13) 0.0317(12) 0.0034(10) -0.0011(9) 0.0082(9) O1 0.0538(12) 0.0347(10) 0.0548(12) 0.0057(9) 0.0003(9) 0.0201(9) C24 0.0268(12) 0.0413(14) 0.0454(14) 0.0189(11) 0.0003(10) 0.0066(10) O2 0.0400(11) 0.0821(16) 0.0607(14) 0.0445(13) -0.0051(10) 0.0110(11) C25 0.0262(11) 0.0351(12) 0.0370(13) 0.0008(10) -0.0036(10) 0.0109(10) O3 0.0362(10) 0.0683(14) 0.0396(11) -0.0068(9) 0.0006(8) 0.0246(10) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Co1 . C1 . 1.961(2) yes Co1 . C22 . 2.071(2) yes Co1 . C23 . 1.770(2) yes Co1 . C24 . 1.790(3) yes Co1 . C25 . 1.774(3) yes C1 . N1 . 1.367(3) yes C1 . N2 . 1.368(3) yes N1 . C2 . 1.389(3) yes N1 . C4 . 1.440(3) yes C2 . C3 . 1.351(3) yes C2 . H21 . 1.000 no C3 . N2 . 1.387(3) yes C3 . H31 . 1.000 no N2 . C13 . 1.444(3) yes C4 . C5 . 1.398(3) yes C4 . C9 . 1.398(3) yes C5 . C6 . 1.393(4) yes C5 . C10 . 1.510(4) yes C6 . C7 . 1.387(4) yes C6 . H61 . 1.000 no C7 . C8 . 1.390(4) yes C7 . C11 . 1.516(4) yes C8 . C9 . 1.390(3) yes C8 . H81 . 1.000 no C9 . C12 . 1.502(4) yes C10 . H101 . 1.000 no C10 . H102 . 1.000 no C10 . H103 . 1.000 no C11 . H111 . 1.000 no C11 . H112 . 1.000 no C11 . H113 . 1.000 no C12 . H121 . 1.000 no C12 . H122 . 1.000 no C12 . H123 . 1.000 no C13 . C14 . 1.398(3) yes C13 . C18 . 1.399(3) yes C14 . C15 . 1.397(3) yes C14 . C19 . 1.505(4) yes C15 . C16 . 1.390(4) yes C15 . H151 . 1.000 no C16 . C17 . 1.395(4) yes C16 . C20 . 1.512(3) yes C17 . C18 . 1.396(3) yes C17 . H171 . 1.000 no C18 . C21 . 1.498(3) yes C19 . H191 . 1.000 no C19 . H192 . 1.000 no C19 . H193 . 1.000 no C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 1.000 no C22 . H1 . 0.99(3) no C22 . H2 . 0.93(4) no C22 . H3 . 0.95(3) no C23 . O1 . 1.145(3) yes C24 . O2 . 1.148(3) yes C25 . O3 . 1.154(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . Co1 . C22 . 176.28(11) yes C1 . Co1 . C23 . 93.92(10) yes C22 . Co1 . C23 . 82.55(11) yes C1 . Co1 . C24 . 99.91(10) yes C22 . Co1 . C24 . 81.05(11) yes C23 . Co1 . C24 . 121.24(12) yes C1 . Co1 . C25 . 99.78(10) yes C22 . Co1 . C25 . 82.84(11) yes C23 . Co1 . C25 . 115.43(12) yes C24 . Co1 . C25 . 117.79(12) yes Co1 . C1 . N1 . 128.06(16) yes Co1 . C1 . N2 . 128.59(16) yes N1 . C1 . N2 . 103.09(18) yes C1 . N1 . C2 . 111.92(19) yes C1 . N1 . C4 . 126.61(19) yes C2 . N1 . C4 . 120.72(19) yes N1 . C2 . C3 . 106.4(2) yes N1 . C2 . H21 . 126.781 no C3 . C2 . H21 . 126.781 no C2 . C3 . N2 . 106.6(2) yes C2 . C3 . H31 . 126.679 no N2 . C3 . H31 . 126.679 no C1 . N2 . C3 . 111.90(19) yes C1 . N2 . C13 . 126.68(18) yes C3 . N2 . C13 . 121.34(19) yes N1 . C4 . C5 . 120.3(2) yes N1 . C4 . C9 . 117.4(2) yes C5 . C4 . C9 . 122.2(2) yes C4 . C5 . C6 . 117.5(2) yes C4 . C5 . C10 . 121.3(2) yes C6 . C5 . C10 . 121.2(2) yes C5 . C6 . C7 . 122.0(2) yes C5 . C6 . H61 . 119.006 no C7 . C6 . H61 . 119.006 no C6 . C7 . C8 . 118.8(2) yes C6 . C7 . C11 . 121.3(3) yes C8 . C7 . C11 . 119.8(3) yes C7 . C8 . C9 . 121.5(2) yes C7 . C8 . H81 . 119.259 no C9 . C8 . H81 . 119.259 no C4 . C9 . C8 . 118.0(2) yes C4 . C9 . C12 . 120.8(2) yes C8 . C9 . C12 . 121.2(2) yes C5 . C10 . H101 . 109.467 no C5 . C10 . H102 . 109.467 no H101 . C10 . H102 . 109.476 no C5 . C10 . H103 . 109.467 no H101 . C10 . H103 . 109.476 no H102 . C10 . H103 . 109.476 no C7 . C11 . H111 . 109.467 no C7 . C11 . H112 . 109.467 no H111 . C11 . H112 . 109.476 no C7 . C11 . H113 . 109.467 no H111 . C11 . H113 . 109.476 no H112 . C11 . H113 . 109.476 no C9 . C12 . H121 . 109.467 no C9 . C12 . H122 . 109.467 no H121 . C12 . H122 . 109.476 no C9 . C12 . H123 . 109.467 no H121 . C12 . H123 . 109.476 no H122 . C12 . H123 . 109.476 no N2 . C13 . C14 . 119.5(2) yes N2 . C13 . C18 . 118.0(2) yes C14 . C13 . C18 . 122.4(2) yes C13 . C14 . C15 . 117.7(2) yes C13 . C14 . C19 . 122.0(2) yes C15 . C14 . C19 . 120.4(2) yes C14 . C15 . C16 . 121.8(2) yes C14 . C15 . H151 . 119.104 no C16 . C15 . H151 . 119.104 no C15 . C16 . C17 . 118.7(2) yes C15 . C16 . C20 . 120.9(2) yes C17 . C16 . C20 . 120.3(3) yes C16 . C17 . C18 . 121.7(2) yes C16 . C17 . H171 . 119.127 no C18 . C17 . H171 . 119.127 no C13 . C18 . C17 . 117.6(2) yes C13 . C18 . C21 . 121.9(2) yes C17 . C18 . C21 . 120.5(2) yes C14 . C19 . H191 . 109.467 no C14 . C19 . H192 . 109.467 no H191 . C19 . H192 . 109.476 no C14 . C19 . H193 . 109.467 no H191 . C19 . H193 . 109.476 no H192 . C19 . H193 . 109.476 no C16 . C20 . H201 . 109.467 no C16 . C20 . H202 . 109.467 no H201 . C20 . H202 . 109.476 no C16 . C20 . H203 . 109.467 no H201 . C20 . H203 . 109.476 no H202 . C20 . H203 . 109.476 no C18 . C21 . H211 . 109.467 no C18 . C21 . H212 . 109.467 no H211 . C21 . H212 . 109.476 no C18 . C21 . H213 . 109.467 no H211 . C21 . H213 . 109.476 no H212 . C21 . H213 . 109.476 no Co1 . C22 . H1 . 110.0(19) no Co1 . C22 . H2 . 109(2) no H1 . C22 . H2 . 108(3) no Co1 . C22 . H3 . 111.8(20) no H1 . C22 . H3 . 109(3) no H2 . C22 . H3 . 108(3) no Co1 . C23 . O1 . 173.2(2) yes Co1 . C24 . O2 . 168.7(2) yes Co1 . C25 . O3 . 170.8(2) yes # Attachment 'compound2.cif' data_arc1039 _database_code_depnum_ccdc_archive 'CCDC 291791' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_special_details ; All hydrogen atoms were positioned geometrically, the preferred orientations of the methyl groups having been identified previously by examination of a difference Fourier map. ; #============================================================= _cell_length_a 8.6117(2) _cell_angle_alpha 90 _cell_length_b 33.0497(5) _cell_angle_beta 112.0508(6) _cell_length_c 9.2569(2) _cell_angle_gamma 90 _cell_volume 2441.92(9) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'Co ' 0.3494 0.9721 12.2841 4.2791 7.3409 0.2784 4.0034 13.5359 2.3488 71.1692 1.0118 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C26 H27 Co1 N2 O4 ' _chemical_formula_moiety ' C26 H27 Co1 N2 O4 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 490.44 _cell_measurement_reflns_used 20344 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' fragment ' _exptl_crystal_colour ' pale yellow ' _exptl_crystal_size_min 0.14 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_max 0.26 _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.736 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.83 _exptl_absorpt_correction_T_max 0.90 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 20344 _reflns_number_total 5525 #5632 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.041 _diffrn_reflns_theta_min 5.100 _diffrn_reflns_theta_max 27.495 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.495 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min -11 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 42 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _refine_diff_density_min -0.25 _refine_diff_density_max 0.39 _refine_ls_number_reflns 3569 _refine_ls_number_restraints 0 _refine_ls_number_parameters 298 #_refine_ls_R_factor_ref 0.0344 _refine_ls_wR_factor_ref 0.0383 _refine_ls_goodness_of_fit_ref 1.1048 #_reflns_number_all 5525 _refine_ls_R_factor_all 0.0652 _refine_ls_wR_factor_all 0.0584 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 3569 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_gt 0.0383 _refine_ls_shift/su_max 0.005340 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.675 0.020 0.379 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type Co1 Co 0.31129(4) 0.365446(9) 0.09053(3) 0.0219 1.0000 Uani C1 C 0.4636(3) 0.38299(7) 0.3041(2) 0.0237 1.0000 Uani N1 N 0.6079(2) 0.36501(6) 0.4009(2) 0.0267 1.0000 Uani C2 C 0.6948(3) 0.38915(8) 0.5288(3) 0.0363 1.0000 Uani C3 C 0.6043(3) 0.42280(8) 0.5140(3) 0.0379 1.0000 Uani N2 N 0.4636(2) 0.41897(6) 0.3773(2) 0.0277 1.0000 Uani C4 C 0.6608(3) 0.32395(7) 0.3906(3) 0.0280 1.0000 Uani C5 C 0.7821(3) 0.31672(8) 0.3271(3) 0.0346 1.0000 Uani C6 C 0.8356(3) 0.27715(9) 0.3273(3) 0.0398 1.0000 Uani C7 C 0.7731(3) 0.24541(8) 0.3875(3) 0.0394 1.0000 Uani C8 C 0.6542(3) 0.25385(8) 0.4511(3) 0.0375 1.0000 Uani C9 C 0.5980(3) 0.29333(7) 0.4564(3) 0.0304 1.0000 Uani C10 C 0.8512(4) 0.35036(11) 0.2592(4) 0.0520 1.0000 Uani C11 C 0.8335(4) 0.20276(10) 0.3840(4) 0.0552 1.0000 Uani C12 C 0.4730(3) 0.30172(9) 0.5310(3) 0.0400 1.0000 Uani C13 C 0.3254(3) 0.44688(7) 0.3377(2) 0.0259 1.0000 Uani C14 C 0.3172(3) 0.47978(7) 0.2409(3) 0.0276 1.0000 Uani C15 C 0.1775(3) 0.50507(7) 0.2017(3) 0.0281 1.0000 Uani C16 C 0.0529(3) 0.49866(7) 0.2605(2) 0.0278 1.0000 Uani C17 C 0.0702(3) 0.46666(7) 0.3631(3) 0.0306 1.0000 Uani C18 C 0.2063(3) 0.44034(7) 0.4038(3) 0.0285 1.0000 Uani C19 C 0.4560(3) 0.48849(9) 0.1839(3) 0.0420 1.0000 Uani C20 C -0.0982(4) 0.52593(8) 0.2148(3) 0.0377 1.0000 Uani C21 C 0.2235(4) 0.40542(8) 0.5140(3) 0.0404 1.0000 Uani C22 C 0.1827(3) 0.35017(7) -0.1337(2) 0.0272 1.0000 Uani C23 C 0.2442(4) 0.31519(10) -0.2022(3) 0.0496 1.0000 Uani O1 O 0.0616(2) 0.36865(5) -0.21713(18) 0.0342 1.0000 Uani C24 C 0.4467(3) 0.38771(8) 0.0089(3) 0.0347 1.0000 Uani O2 O 0.5295(3) 0.40227(8) -0.0498(3) 0.0584 1.0000 Uani C25 C 0.2997(3) 0.31323(8) 0.1361(3) 0.0324 1.0000 Uani O3 O 0.2774(3) 0.27989(6) 0.1546(2) 0.0511 1.0000 Uani C26 C 0.1252(3) 0.39337(7) 0.0782(2) 0.0265 1.0000 Uani O4 O -0.0011(2) 0.40832(5) 0.0545(2) 0.0354 1.0000 Uani H21 H 0.8036 0.3826 0.6149 0.0390 1.0000 Uiso H31 H 0.6323 0.4463 0.5873 0.0399 1.0000 Uiso H61 H 0.9223 0.2713 0.2824 0.0466 1.0000 Uiso H81 H 0.6076 0.2312 0.4941 0.0412 1.0000 Uiso H101 H 0.9359 0.3391 0.2201 0.0652 1.0000 Uiso H102 H 0.9056 0.3711 0.3415 0.0652 1.0000 Uiso H103 H 0.7580 0.3632 0.1710 0.0652 1.0000 Uiso H111 H 0.7752 0.1841 0.4321 0.0600 1.0000 Uiso H112 H 0.9571 0.2014 0.4439 0.0600 1.0000 Uiso H113 H 0.8082 0.1945 0.2735 0.0600 1.0000 Uiso H121 H 0.4440 0.2759 0.5711 0.0487 1.0000 Uiso H122 H 0.5227 0.3211 0.6195 0.0487 1.0000 Uiso H123 H 0.3694 0.3138 0.4520 0.0487 1.0000 Uiso H151 H 0.1669 0.5283 0.1295 0.0326 1.0000 Uiso H171 H -0.0171 0.4625 0.4086 0.0378 1.0000 Uiso H191 H 0.4274 0.5132 0.1164 0.0521 1.0000 Uiso H192 H 0.5628 0.4932 0.2752 0.0521 1.0000 Uiso H193 H 0.4702 0.4649 0.1224 0.0521 1.0000 Uiso H201 H -0.1737 0.5168 0.2682 0.0459 1.0000 Uiso H202 H -0.0613 0.5544 0.2467 0.0459 1.0000 Uiso H203 H -0.1600 0.5248 0.0994 0.0459 1.0000 Uiso H211 H 0.1270 0.4056 0.5493 0.0504 1.0000 Uiso H212 H 0.3307 0.4082 0.6065 0.0504 1.0000 Uiso H213 H 0.2240 0.3794 0.4593 0.0504 1.0000 Uiso H231 H 0.1681 0.3113 -0.3135 0.0572 1.0000 Uiso H232 H 0.3603 0.3210 -0.1967 0.0572 1.0000 Uiso H233 H 0.2452 0.2900 -0.1419 0.0572 1.0000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.02083(14) 0.02425(14) 0.01836(13) 0.00064(12) 0.00461(10) 0.00059(13) C1 0.0245(11) 0.0236(10) 0.0219(10) 0.0016(8) 0.0075(9) -0.0002(8) N1 0.0227(9) 0.0294(9) 0.0214(8) -0.0027(8) 0.0007(7) 0.0002(8) C2 0.0301(12) 0.0395(14) 0.0280(12) -0.0055(10) -0.0020(10) 0.0013(10) C3 0.0335(13) 0.0379(14) 0.0284(12) -0.0104(10) -0.0043(10) -0.0002(11) N2 0.0249(10) 0.0288(10) 0.0236(9) -0.0036(7) 0.0024(7) 0.0002(8) C4 0.0236(12) 0.0293(11) 0.0239(11) -0.0012(9) 0.0007(9) 0.0039(9) C5 0.0256(12) 0.0451(15) 0.0294(12) 0.0021(10) 0.0060(10) 0.0044(10) C6 0.0274(13) 0.0539(17) 0.0351(13) -0.0033(12) 0.0082(10) 0.0119(12) C7 0.0352(13) 0.0404(15) 0.0310(12) -0.0035(11) -0.0007(10) 0.0108(11) C8 0.0352(13) 0.0371(14) 0.0308(12) 0.0054(10) 0.0015(10) 0.0060(11) C9 0.0280(12) 0.0362(13) 0.0218(11) 0.0019(9) 0.0034(9) 0.0059(10) C10 0.0388(16) 0.0603(19) 0.0638(19) 0.0074(15) 0.0272(15) 0.0021(14) C11 0.0500(18) 0.0462(17) 0.0539(18) -0.0054(14) 0.0016(14) 0.0210(14) C12 0.0375(14) 0.0492(16) 0.0350(13) 0.0107(11) 0.0156(11) 0.0090(12) C13 0.0253(11) 0.0255(11) 0.0226(10) -0.0068(8) 0.0040(8) 0.0012(8) C14 0.0280(11) 0.0254(11) 0.0275(11) -0.0044(9) 0.0083(9) -0.0046(9) C15 0.0355(13) 0.0219(11) 0.0241(10) -0.0018(8) 0.0080(9) -0.0027(9) C16 0.0297(12) 0.0286(12) 0.0222(10) -0.0059(8) 0.0064(9) 0.0025(9) C17 0.0374(13) 0.0303(12) 0.0268(11) -0.0027(9) 0.0153(10) 0.0016(10) C18 0.0370(13) 0.0264(11) 0.0214(10) -0.0023(9) 0.0104(9) 0.0017(10) C19 0.0353(14) 0.0423(15) 0.0526(16) 0.0061(12) 0.0212(13) -0.0037(12) C20 0.0433(14) 0.0358(14) 0.0357(13) 0.0025(11) 0.0168(11) 0.0117(11) C21 0.0561(17) 0.0360(14) 0.0339(13) 0.0092(11) 0.0224(12) 0.0098(12) C22 0.0277(12) 0.0295(11) 0.0223(10) -0.0004(8) 0.0071(9) -0.0043(9) C23 0.0579(19) 0.0583(19) 0.0267(12) -0.0086(12) 0.0090(12) 0.0186(15) O1 0.0308(9) 0.0382(10) 0.0232(7) 0.0022(7) -0.0019(7) 0.0024(8) C24 0.0306(12) 0.0457(15) 0.0251(11) 0.0004(10) 0.0073(10) -0.0012(11) O2 0.0490(12) 0.0839(17) 0.0498(12) 0.0099(11) 0.0271(11) -0.0141(11) C25 0.0311(12) 0.0354(14) 0.0210(10) -0.0017(9) -0.0012(9) 0.0032(10) O3 0.0650(14) 0.0264(10) 0.0431(11) 0.0039(8) -0.0013(10) -0.0040(9) C26 0.0286(12) 0.0286(11) 0.0202(10) 0.0002(8) 0.0066(9) -0.0021(9) O4 0.0261(9) 0.0417(10) 0.0357(9) -0.0018(7) 0.0083(7) 0.0058(7) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Co1 . C1 . 2.004(2) yes Co1 . C22 . 2.016(2) yes Co1 . C24 . 1.770(3) yes Co1 . C25 . 1.788(3) yes Co1 . C26 . 1.815(2) yes C1 . N1 . 1.365(3) yes C1 . N2 . 1.369(3) yes N1 . C2 . 1.390(3) yes N1 . C4 . 1.446(3) yes C2 . C3 . 1.335(4) yes C2 . H21 . 1.000 no C3 . N2 . 1.390(3) yes C3 . H31 . 1.000 no N2 . C13 . 1.441(3) yes C4 . C5 . 1.398(3) yes C4 . C9 . 1.391(3) yes C5 . C6 . 1.387(4) yes C5 . C10 . 1.505(4) yes C6 . C7 . 1.388(4) yes C6 . H61 . 1.000 no C7 . C8 . 1.388(4) yes C7 . C11 . 1.507(4) yes C8 . C9 . 1.399(4) yes C8 . H81 . 1.000 no C9 . C12 . 1.507(4) yes C10 . H101 . 1.000 no C10 . H102 . 1.000 no C10 . H103 . 1.000 no C11 . H111 . 1.000 no C11 . H112 . 1.000 no C11 . H113 . 1.000 no C12 . H121 . 1.000 no C12 . H122 . 1.000 no C12 . H123 . 1.000 no C13 . C14 . 1.394(3) yes C13 . C18 . 1.394(3) yes C14 . C15 . 1.396(3) yes C14 . C19 . 1.504(3) yes C15 . C16 . 1.390(3) yes C15 . H151 . 1.000 no C16 . C17 . 1.391(3) yes C16 . C20 . 1.508(3) yes C17 . C18 . 1.394(3) yes C17 . H171 . 1.000 no C18 . C21 . 1.511(3) yes C19 . H191 . 1.000 no C19 . H192 . 1.000 no C19 . H193 . 1.000 no C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 1.000 no C22 . C23 . 1.507(4) yes C22 . O1 . 1.205(3) yes C23 . H231 . 1.000 no C23 . H232 . 1.000 no C23 . H233 . 1.000 no C24 . O2 . 1.151(3) yes C25 . O3 . 1.142(3) yes C26 . O4 . 1.138(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . Co1 . C22 . 172.34(9) yes C1 . Co1 . C24 . 90.49(10) yes C22 . Co1 . C24 . 81.95(10) yes C1 . Co1 . C25 . 96.92(9) yes C22 . Co1 . C25 . 86.76(10) yes C24 . Co1 . C25 . 127.29(12) yes C1 . Co1 . C26 . 98.65(9) yes C22 . Co1 . C26 . 86.08(10) yes C24 . Co1 . C26 . 117.99(11) yes C25 . Co1 . C26 . 112.29(11) yes Co1 . C1 . N1 . 128.23(16) yes Co1 . C1 . N2 . 128.18(16) yes N1 . C1 . N2 . 102.83(18) yes C1 . N1 . C2 . 112.04(19) yes C1 . N1 . C4 . 126.63(18) yes C2 . N1 . C4 . 120.85(18) yes N1 . C2 . C3 . 106.5(2) yes N1 . C2 . H21 . 126.754 no C3 . C2 . H21 . 126.755 no C2 . C3 . N2 . 107.0(2) yes C2 . C3 . H31 . 126.478 no N2 . C3 . H31 . 126.478 no C1 . N2 . C3 . 111.59(19) yes C1 . N2 . C13 . 125.71(18) yes C3 . N2 . C13 . 121.86(19) yes N1 . C4 . C5 . 119.4(2) yes N1 . C4 . C9 . 118.0(2) yes C5 . C4 . C9 . 122.3(2) yes C4 . C5 . C6 . 117.5(2) yes C4 . C5 . C10 . 121.6(2) yes C6 . C5 . C10 . 120.9(2) yes C5 . C6 . C7 . 122.3(2) yes C5 . C6 . H61 . 118.857 no C7 . C6 . H61 . 118.856 no C6 . C7 . C8 . 118.6(2) yes C6 . C7 . C11 . 120.6(3) yes C8 . C7 . C11 . 120.8(3) yes C7 . C8 . C9 . 121.5(3) yes C7 . C8 . H81 . 119.258 no C9 . C8 . H81 . 119.257 no C4 . C9 . C8 . 117.8(2) yes C4 . C9 . C12 . 121.9(2) yes C8 . C9 . C12 . 120.3(2) yes C5 . C10 . H101 . 109.466 no C5 . C10 . H102 . 109.466 no H101 . C10 . H102 . 109.476 no C5 . C10 . H103 . 109.466 no H101 . C10 . H103 . 109.476 no H102 . C10 . H103 . 109.476 no C7 . C11 . H111 . 109.467 no C7 . C11 . H112 . 109.465 no H111 . C11 . H112 . 109.477 no C7 . C11 . H113 . 109.466 no H111 . C11 . H113 . 109.477 no H112 . C11 . H113 . 109.475 no C9 . C12 . H121 . 109.467 no C9 . C12 . H122 . 109.467 no H121 . C12 . H122 . 109.476 no C9 . C12 . H123 . 109.466 no H121 . C12 . H123 . 109.476 no H122 . C12 . H123 . 109.476 no N2 . C13 . C14 . 120.0(2) yes N2 . C13 . C18 . 117.6(2) yes C14 . C13 . C18 . 122.4(2) yes C13 . C14 . C15 . 117.7(2) yes C13 . C14 . C19 . 121.3(2) yes C15 . C14 . C19 . 121.0(2) yes C14 . C15 . C16 . 121.6(2) yes C14 . C15 . H151 . 119.218 no C16 . C15 . H151 . 119.218 no C15 . C16 . C17 . 118.9(2) yes C15 . C16 . C20 . 120.8(2) yes C17 . C16 . C20 . 120.4(2) yes C16 . C17 . C18 . 121.5(2) yes C16 . C17 . H171 . 119.250 no C18 . C17 . H171 . 119.250 no C13 . C18 . C17 . 117.8(2) yes C13 . C18 . C21 . 120.9(2) yes C17 . C18 . C21 . 121.2(2) yes C14 . C19 . H191 . 109.467 no C14 . C19 . H192 . 109.467 no H191 . C19 . H192 . 109.475 no C14 . C19 . H193 . 109.467 no H191 . C19 . H193 . 109.476 no H192 . C19 . H193 . 109.476 no C16 . C20 . H201 . 109.467 no C16 . C20 . H202 . 109.467 no H201 . C20 . H202 . 109.475 no C16 . C20 . H203 . 109.467 no H201 . C20 . H203 . 109.476 no H202 . C20 . H203 . 109.476 no C18 . C21 . H211 . 109.467 no C18 . C21 . H212 . 109.466 no H211 . C21 . H212 . 109.476 no C18 . C21 . H213 . 109.466 no H211 . C21 . H213 . 109.476 no H212 . C21 . H213 . 109.476 no Co1 . C22 . C23 . 118.77(17) yes Co1 . C22 . O1 . 122.81(18) yes C23 . C22 . O1 . 118.4(2) yes C22 . C23 . H231 . 109.466 no C22 . C23 . H232 . 109.467 no H231 . C23 . H232 . 109.477 no C22 . C23 . H233 . 109.466 no H231 . C23 . H233 . 109.475 no H232 . C23 . H233 . 109.476 no Co1 . C24 . O2 . 177.3(2) yes Co1 . C25 . O3 . 173.5(2) yes Co1 . C26 . O4 . 171.8(2) yes